Charge-air cooler will not return much, unless you are towing\hauling at sustained Boost levels above ~10-12psi.
Your summertime use can qualify for that, but first would be the '97 cooling modifications, with HO waterpump, dual t-stats, 21" D-max fan, and reduced thermo-cut-in fan clutch.

Towing at those upgraded Boost levels will put you on the side of the road more often, waiting for engine coolant temps to cool down, even with charge-air cooler.

Unfortunately, they - all that are available - are unreasonable, because the 6.5 is obsolete, and very few are willing to flog a dead horse.

Kennedy and others sell the Spearco unit, which imo is the most efficient, thermally, of the available kits, which will fit and is relatively easy to install in the '88-up GM truck series.

You might check out the FAQ's for Turbine Doc's pictorial install, and upgrade path, and ronniejoe's dyno runs with similar equipment.

Just remember - the upgrades go hand-in-hand with, and should be based on, the coolant system upgrade.
Late '96 and up trucks got it from the factory for the proposed 215hp upgrade, which never occured.
Imo it was the lack of available space for a practical charge-air cooler that helped to kill the power improvement.

Just get a salvaged cummins or PS core ~$300 and remove the crossbrace and move conderser core toward the radiator(might help keep the leaf build up down). You'd have to plumb it yourself but a muffler shop could bend it out.

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